FeII-catalysed insertion reaction of α-diazocarbonyls into X-H bonds (X = Si, S, N, and O) in dimethyl carbonate as a suitable solvent alternative

Abstract

The insertion reaction of a broad range of diazo compounds into Si-H bonds was found to be efficiently catalysed by Fe(OTf)2 in an emerging green solvent i.e. dimethyl carbonate (DMC). The α-silylated products were obtained in good to excellent yields (up to 95%). Kinetic studies showed that the extrusion of N2 to form an iron carbene intermediate is rate-limiting. The iron-catalysed insertion reaction of methyl α-phenyl-α-diazoacetate into polar X-H bonds (S-H, N-H, and O-H) was also established in DMC.